WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 202130
CAS#: 1070409-31-2 (tris salt)
Description: Palifosfamide, also known as ZIO201, is a synthetic mustard compound with potential antineoplastic activity. An active metabolite of ifosfamide covalently linked to the amino acid lysine for stability, palifosfamide irreversibly alkylates and cross-links DNA through GC base pairs, resulting in irreparable 7-atom inter-strand cross-links; inhibition of DNA replication and cell death follow. Unlike ifosfamide, this agent is not metabolized to acrolein or chloroacetaldehyde, metabolites associated with bladder and CNS toxicities. In addition, because palifosfamide does not require activation by aldehyde dehydrogenase, it may overcome the tumor resistance seen with ifosfamide.
MedKoo Cat#: 202130
Name: Palifosfamide-Tris
CAS#: 1070409-31-2 (tris salt)
Chemical Formula: C8H22Cl2N3O5P
Exact Mass:
Molecular Weight: 342.15
Elemental Analysis: C, 28.08; H, 6.48; Cl, 20.72; N, 12.28; O, 23.38; P, 9.05
Palifosfamide-tris is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.
Related CAS #: 1070409-31-2 (tris salt); 31645-39-3 (free acid)
Synonym: ZIO201; ZIO-201; ZIO 201; IPAM; NSC 297900; NSC-297900; NSC297900; isophosphoramide mustard; Palifosfamide. Palifosfamide tris salt; Trade name: Zymafos.
IUPAC/Chemical Name: N,N'-Bis(2-chloroethyl)phosphorodiamidic acid
InChi Key: BKCJZNIZRWYHBN-UHFFFAOYSA-N
InChi Code: InChI=1S/C4H11Cl2N2O2P/c5-1-3-7-11(9,10)8-4-2-6/h1-4H2,(H3,7,8,9,10)
SMILES Code: O=P(NCCCl)(NCCCl)O.NC(CO)(CO)CO
The following data is based on the product molecular weight 342.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Williams R. Discontinued in 2013: oncology drugs. Expert Opin Investig Drugs. 2015 Jan;24(1):95-110. Epub 2014 Oct 14. PubMed PMID: 25315907.
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4: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Dec;31(10):661-700. PubMed PMID: 20140276.
5: Jung S, Kasper B. Palifosfamide, a bifunctional alkylator for the treatment of sarcomas. IDrugs. 2010 Jan;13(1):38-48. Review. PubMed PMID: 20024846.
6: Hingorani P, Zhang W, Piperdi S, Pressman L, Lin J, Gorlick R, Kolb EA. Preclinical activity of palifosfamide lysine (ZIO-201) in pediatric sarcomas including oxazaphosphorine-resistant osteosarcoma. Cancer Chemother Pharmacol. 2009 Sep;64(4):733-40. doi: 10.1007/s00280-008-0922-4. Epub 2009 Feb 18. PubMed PMID: 19224214.
7: Anderson P, Aguilera D, Pearson M, Woo S. Outpatient chemotherapy plus radiotherapy in sarcomas: improving cancer control with radiosensitizing agents. Cancer Control. 2008 Jan;15(1):38-46. Review. PubMed PMID: 18094659.
Palifosfamide (ZIO-201) is currently developed by ZIOPHARM Oncology, Inc. It is a proprietary stabilized metabolite of ifosfamide. Ifosfamide has been shown to be effective in high doses in treating testicular cancer, sarcoma and lymphoma. Ifosfamide-based treatment generally represents the standard of care for sarcoma; however, it is not approved by the FDA in this indication. Ifosfamide metabolites include acrolein and chloroacetaldehyde, both highly toxic. Preclinical studies have shown that palifosfamide has activity in leukemia and solid tumor cancers. These studies also indicate that palifosfamide has a better safety profile than ifosfamide, likely because the toxic metabolites of ifosfamide, acrolein and chloroacetaldehyde are not present in palifosfamide. We believe the administration of palifosfamide may avoid many of the toxicities of ifosfamide without compromising the activity of the drug. see ZIOPHARM's website: http://www.ziopharm.com/clinical_zio201.php.
